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Rosalee Futch (Kate Bosworth) is a grocery clerk living in rural West Virginia. But even a small-town girl can have big dreams, and Rosalee's is to someday... somehow... meet her big-screen idol Tad Hamilton (Josh Duhamel). The "somehow" arrives in the form of a contest -- the grand prize: a date with Tad Hamilton -- and the "someday" is now. Rosalee wins, much to the chagrin of her best friend and co-worker Pete (Topher Grace), who is deeply, hopelessly -- and secretly -- in love with Rosalee.

The "Win a Date" contest was cooked up by Tad's agent, Richard Levy (Nathan Lane), and his manager, also named Richard Levy (Sean Hayes), to clean up Tad's bad-boy image. Someone should have told them to be careful what you wish for. When Tad meets Rosalee and gets a taste of what he's been missing in the "real world," he decides he wants seconds and moves to West Virginia, turning Rosalee's dream come true into a nightmare for Richard Levy, Richard Levy and, most of all, Pete.